Potassium Carbonate → HCID 68689447, compound
Reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH2:16][N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[CH:22][CH:21]=1Participants
Procedure
A mixture of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.200 g, 1.09 mmol), 4-bromomethyl-biphenyl (0.322 g, 1.303 mmol) and potassium carbonate (0.300 g, 2.17 mol) in dry N, N-dimethyl formamide (6 mL) was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was then partitioned between ethyl acetate (50 mL) and 2 M sodium hydroxide (50 mL). The separated organic phase was washed with 2 M sodium hydroxide (50 mL), water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a colorless syrup (0.42 g). Purification by flash chromatography using a solvent gradient of 0 to 5% ethyl acetate in hexane afforded a white foam that was crystallized from ethyl acetate/hexane to afford the title compound (0.261 g, 68%) as a white crystalline solid, m.p. 135-137° C.
Workup
- customThe reaction mixture was then partitioned between ethyl acetate (50 mL) and 2 M sodium hydroxide (50 mL)
- washThe separated organic phase was washed with 2 M sodium hydroxide (50 mL), water (50 mL) and brine (50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-78941607552c46c1a6760f8a3ddf7a67
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678787B2
Reaction notes
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