Bromide ion → HCID 15979795, compound

HRID 1896472Notes

Reaction equation

HRID 1896472 reaction equation
[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][CH:17]=[CH:18][C:11]=23)[C:6](=[O:19])[CH2:5]1)[CH2:2][CH3:3].[Br-].[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.[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][CH:17]=[CH:18][C:11]=23)[C:6](=[O:19])[CH2:5]1)[CH2:2][CH3:3]

Participants

7

Reactant 5

HCID 259Bromide ion2×HCID 114736554-Bromo-1-(triisopropylsilyl)-7-azaindoleHCID 15979795HCID 15979795, compound2×HCID 49758886HCID 49758886, compoundHCID 53629210HCID 53629210, compound

Product 2

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

Procedure

Synthesis of 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)pyrrolidin-2-one 240. 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-d344c27624b54513aa413ea57cc9cd42
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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