Isobutane → Tert-butyl 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-C]pyridine-1-carboxylate

HRID 1475399Notes

Reaction equation

HRID 1475399 reaction equation
[Br:1]C1C=C(N)C=CN=1.[C:9]([O:13][C:14]([N:16]1[C:24]2[CH:23]=[C:22](Cl)[N:21]=[CH:20][C:19]=2[C:18]([CH3:27])([CH3:26])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(C)(C)C.BrC1C=C(N)C(I)=CN=1.BrC1C=C(NCC(C)=C)C(I)=CN=1.BrC1N=CC2C(C)(C)CNC=2C=1>>[C:9]([O:13][C:14]([N:16]1[C:24]2[CH:23]=[C:22]([Br:1])[N:21]=[CH:20][C:19]=2[C:18]([CH3:27])([CH3:26])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 6

HCID 6360IsobutaneHCID 3464554-Amino-2-bromopyridineHCID 601457042-Bromo-5-iodopyridin-4-amineHCID 86723969tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylateHCID 867240042-Bromo-5-iodo-N-(2-methylallyl)pyridin-4-amineHCID 867240056-bromo-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86724003Tert-butyl 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-C]pyridine-1-carboxylate

Procedure

The title compound was prepared from 2-bromo-pyridin-4-ylamine using analogous methods to those outlined above for 6-chloro-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (Preparations 107-110). Colourless solid. 1H NMR (CDCl3) 8.00 (1H, s), 7.87 (1H, br s), 3.75 (2H, s), 1.59 (9H, br s), 1.39 (6H, s). MS: [M+H−tBu]+ 271, 273. Synthetic intermediates isolated in this process were as follows: 2-Bromo-5-iodo-pyridin-4-ylamine (pale orange solid, 1H NMR (DMSO-d6) 8.18 (1H, s), 6.78 (1H, s), 6.48 (2H, br s); MS: [M+H]+ 299, 301); (2-Bromo-5-iodo-pyridin-4-yl)-(2-methyl-allyl)-amine (pale orange oil, 1H NMR (DMSO-d6) 8.20 (1H, s), 6.52 (1H, s), 6.47 (1H, brt), 4.85 (1H, d), 4.74 (1H, d), 3.82 (2H, d), 1.68 (3H, s); MS: [M+H]+ 353, 355); 6-Bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine (colourless solid, 1H NMR (DMSO-d6) 7.70 (1H, s), 6.73 (1H, br s), 6.47 (1H, s), 3.30 (2H, d), 1.26 (6H, s); MS: [M+H]+ 227, 229).

Workup

  1. customSynthetic intermediates isolated in this process

Sources & evidence

ORD record
ord-5d1c80adc67f41e2a660dd64d551b099
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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