Boronic Acid → 2,6-difluoro-3-(2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-benzaldehyde
Reaction equation
Cl[C:2]1[C:3]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=1.[F:23][C:24]1[C:29]([CH:30]=[O:31])=[C:28]([F:32])[CH:27]=[CH:26][C:25]=1B(O)O.B(O)O>>[F:23][C:24]1[C:25]([C:2]2[C:3]3[CH2:16][CH2:15][N:14]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[C:4]=3[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=2)=[CH:26][CH:27]=[C:28]([F:32])[C:29]=1[CH:30]=[O:31]Participants
4
Reactant 3
Product 1
Procedure
In the same manner as Example 1-B-10, using 4-chloro-2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine, and 2,4-difluoro-3-formylphenylboronic acid as a boronic acid, 2,6-difluoro-3-(2-morpholin-4-yl-7-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-benzaldehyde was obtained. Methanol and sodium borohydride were added, which was stirred at room temperature for 1 hour, followed by elution with 2M ammonia methanol solution through SCX resin and then concentration. Purification by preparative TLC afforded the desired compound as a colorless solid.
Sources & evidence
- ORD record
- ord-0f21c22210c14fda9fb1127a206ba5ee
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022205B2
Reaction notes
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