Bromide ion → HCID 15979795, compound

HRID 1924335Notes

Reaction equation

HRID 1924335 reaction equation
[Br-].[CH2:2]([CH:5]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)[C:7](=[O:20])[CH2:6]1)[CH2:3][CH3:4].[Br:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[N:28]([Si](C(C)C)(C(C)C)C(C)C)[CH:29]=[CH:30][C:23]=12.C([Si](C(C)C)(C(C)C)N1C2N=CC=C(C=O)C=2C=C1)(C)C.C(C1CN(CC2C=CN=C3N([Si](C(C)C)(C(C)C)C(C)C)C=CC=23)C(=O)C1)CC>>[Br:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12.[CH2:2]([CH:5]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)[C:7](=[O:20])[CH2:6]1)[CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 259Bromide ion2×HCID 114736554-Bromo-1-(triisopropylsilyl)-7-azaindoleHCID 15979795HCID 15979795, compoundHCID 49758886HCID 49758886, compoundHCID 53629210HCID 53629210, compound

Product 2

HCID 15979795HCID 15979795, compoundHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Procedure

The further transformation of bromide x258 into the target product 240 is carried out in complete accordance with the transformation of bromide b191-1 into product ucb-108891-1 as described in examples 79.2 to 79.4. The yields are similar for intermediates 4-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine x259, 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde x260 and 4-propyl-1-{[1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methyl}pyrrolidin-2-one x261. As a result, 1.0 g (5.1 mmol) of 4-bromo-1H-pyrrolo[2,3-b]pyridine x258 affords 0.45 g of 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)pyrrolidin-2-one 240.

Sources & evidence

ORD record
ord-fd531f7784024c009abc2f578d91bde5
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

Loading…