1-Bromo-3-chloropropane → HCID 67454924, compound

HRID 1713321Notes

Reaction equation

HRID 1713321 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][C:24]3[N:25]([C:56]4[N:57]=[CH:58][N:59]=[C:60]([NH2:63])[C:61]=4[N:62]=3)[C@@H:26]3[O:55][C@H:45]([CH2:46][O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[C@@H:36]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[C@H:27]3[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1C=CC=C[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].BrCCC[Cl:74]>CO.[Pd]>[Si:29]([O:28][C@@H:27]1[C@H:36]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[C@@H:45]([CH2:46][O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[O:55][C@H:26]1[N:25]1[C:56]2[N:57]=[CH:58][N:59]=[C:60]([NH2:63])[C:61]=2[N:62]=[C:24]1[NH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][Cl:74])[CH:10]=2)=[CH:16][CH:17]=1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 87407424HCID 87407424, compound

Product 1

HCID 67454924HCID 67454924, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8-[2-(3′-benzyloxybiphenyl-4-yl)ethyl-amino]-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.27 g) and 10% palladium-on carbon (56.2 wt % H2O, 0.12 g) in methanol (5 mL) was stirred at room temperature for 3 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure. To a solution of the residue obtained in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.12 g). Then 1-bromo-3-chloropropane (0.07 mL) was added, and the resulting mixture was stirred at 40° C. for 42 hours. The reaction mixture was partitioned between ethyl acetate (45 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.19 g).

Workup

  1. filtrationThe insoluble material was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customTo a solution of the residue obtained in N,N-dimethylformamide (3 mL)
  4. stirringthe resulting mixture was stirred at 40° C. for 42 hours
  5. customThe reaction mixture was partitioned between ethyl acetate (45 mL) and water (10 mL)
  6. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-680e7533ab034ce0920f3070111426ca
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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