Water → HCID 66997922, compound

HRID 559193Notes

Reaction equation

HRID 559193 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:27](=[O:28])[N:26]([CH3:29])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=1)=[CH:16][CH:15]=3.[N:30]#[C:31]Br.C(N(CC)CC)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:27](=[O:28])[N:26]([CH3:29])[C:12]2[N:13]([C:31]#[N:30])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=1)=[CH:16][CH:15]=3

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 66998095HCID 66998095, compound

Product 1

HCID 66997922HCID 66997922, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

460 mg (1.09 mmol) of compound from Example 37 above, 3-(2,4-dichlorophenyl)-1-methyl-6-(1-methyl-1H-pyrazol-3-yl)-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one are dissolved in 50 ml of CH2Cl2. 576 mg (5.43 mmol) of CNBr, 44 mg (0.36 mmol) of DMAP and then 308 μl (2.17 mmol) of triethylamine are added. The mixture is stirred at ambient temperature for 18 h. H2O is added, the mixture is extracted with CH2Cl2, and the organic phase is dried over MgSO4, filtered and concentrated, and purification is carried out on a silica column, elution being carried out with EtOAc/50% cyclohexane.

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialthe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurification
  6. washis carried out on a silica column, elution

Sources & evidence

ORD record
ord-953e3296ab0f4b2bb0b58f56b932da82
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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