Sodium Carbonate → 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-ol

HRID 549043Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:21]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:28]1([CH3:31])[CH:27]=[CH:26][C:25]([S:22]([N:21]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=[C:13]2[C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=3)[N:8]([CH3:12])[CH:7]=2)(=[O:24])=[O:23])=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [24.5 g, Reference Example 13(b)] in dichloromethane (500 mL), at 0° C. under an atmosphere of nitrogen, was added a solution of boron tribromide in dichloromethane (60 mL, 1.0M) and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was allowed to warm slowly to ambient temperature and stirring continued for 12 hours. A solution of sodium carbonate (1M, 250 mL) was added to the mixture and stirring was continued vigorously for 3 hours. The precipitated solid was collected by filtration, washed with dichloromethane (100 mL) and dried to give the title compound (18.75 g) as a colourless solid, m.p. 256-257° C. MS: 418 (MH+).

Workup

temperatureto warm slowly to ambient temperature
stirringstirring
waitcontinued for 12 hours
stirringstirring
waitwas continued vigorously for 3 hours
filtrationThe precipitated solid was collected by filtration
washwashed with dichloromethane (100 mL)
customdried

Sources & evidence

ORD record: ord-dbda193020dc4eac803ae0d7de7d6cf4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943616B2

Reaction notes

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