3-Fluoro-1-propanol → HCID 53339379, compound

HRID 2361516Notes

Reaction equation

HRID 2361516 reaction equation
[F:1][CH2:2][CH2:3][CH2:4]O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:28][O:29][C:30]1[CH:49]=[CH:48][C:33]2[N:34]=[C:35]3[N:40]=[C:39]([C:41]4[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=4)[CH:38]=[CH:37][N:36]3[C:32]=2[CH:31]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[F:1][CH2:2][CH2:3][CH2:4][NH:45][C:44]1[CH:46]=[CH:47][C:41]([C:39]2[CH:38]=[CH:37][N:36]3[C:32]4[CH:31]=[C:30]([O:29][CH3:28])[CH:49]=[CH:48][C:33]=4[N:34]=[C:35]3[N:40]=2)=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 680423-Fluoro-1-propanolHCID 159087TriacetoxyperiodinaneHCID 5049666Sodium triacetoxyborohydrideHCID 67301485HCID 67301485, compound

Product 1

HCID 53339379HCID 53339379, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-fluoropropan-1-ol (5 mg, 0.05 mmol) in 0.3 mL o DCM at rt was added Dess-Martin reagent (42 mg, 0.1 mmol). The mixture was stirred for 1 h at rt and 0.3 mL of DCE was added. It was filtered through a cotton pad into a stirred mixture of 4-(7-methoxybenzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline (5 mg, 0.017 mmol, prepared following General Experiment Procedures Q and R) and NaBH(AcO)3 (42 mg, 0.2 mmol) in 0.3 mL of DCE. The reaction was vigorously stirred for 5 min and quenched by adding Na2CO3 (2 mL, saturated). The mixture was extracted with EtOAc (3×5 mL) and the combined organic phase was washed with water (2×10 mL) and dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by reversed phase HPLC (TFA buffered water/MeCN) to afford the title compound as an orange solid (5 mg, 53%, TFA salt). MS (ESI) m/z [M+H]+351.

Workup

  1. stirringThe reaction was vigorously stirred for 5 min
  2. customquenched
  3. additionby adding Na2CO3 (2 mL, saturated)
  4. extractionThe mixture was extracted with EtOAc (3×5 mL)
  5. washthe combined organic phase was washed with water (2×10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by reversed phase HPLC (TFA buffered water/MeCN)

Sources & evidence

ORD record
ord-73e88b5ef78046a69d55bdf4fc626e60
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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