Dimethylformamide → HCID 178511843, compound

HRID 2254103Notes

Reaction equation

HRID 2254103 reaction equation
[N:1]#[C:2]Br.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]23N(C)[CH:17]([CH2:18][CH2:19]2)[CH2:16][CH2:15][CH2:14]3)=[N:5]1.C(=O)([O-])[O-].[K+].[K+].C[N:29](C)C=O>O>[C:2]([N:1]1[CH:15]2[CH2:16][CH2:17][CH:18]1[CH2:19][CH:13]([C:6]1[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][N:5]=1)[CH2:14]2)#[N:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 178479865HCID 178479865, compound

Product 1

HCID 178511843HCID 178511843, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyanogen bromide (10 g) was added in one portion to a suspension of (1H-indazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane (11 g) and potassium carbonate (12 g) in dimethylformamide (250 ml) at room temperature. The mixture was stirred for 3 hours after which it was diluted with water, and extracted with ethyl acetate (3×300 ml). The combined organic solution was washed with brine, dried over MgSO4, filtered and concentrated to leave 11 g of an oil. Crystallization from DCM:hexane provided 3.1 gm of a solid, m.p. 199°-201° C. Recrystallization from ethanol gave 1.15 g of crystals, m.p. 201°-202° C.

Workup

  1. extractionextracted with ethyl acetate (3×300 ml)
  2. washThe combined organic solution was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-849cb5bcb9544b689d0a2654346d7aec
Source dataset
uspto-grants-1993_08
Patent number
US05234931

Reaction notes

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