Hydrogen Bromide → HCID 59700160, compound

HRID 901366Notes

Reaction equation

HRID 901366 reaction equation
C([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:8]=1)(C)(C)C.Br.SCC(O)=O>C(O)(=O)C>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:30])=[O:5])[CH:14]=2)[NH:19][CH:20]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1133Thioglycolic AcidHCID 67061262HCID 67061262, compound

Product 1

HCID 59700160HCID 59700160, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid tert-butyl ester (1.97 g, 4.92 mmol) in acetic acid (4 mL) was added dropwise a premixed solution of hydrogen bromide (33% wt in acetic acid) (889 uL, 4.92 mmol) and mercaptoacetic acid (444 uL, 6.39 mmol). The sides of the flask were rinsed with additional acetic acid (3 mL) and the reaction solution was stirred at ambient temperature for 10 minutes whereupon the product began to precipitate out of solution. The reaction was stirred for an additional hour at ambient temperature. The precipitate was filtered and rinsed well with acetic acid and diethyl ether, affording the title compound as a bright yellow solid (448 mg, 67% yield). 1H NMR (500 MHz, d6-DMSO) δ 12.03 (br s, 1H), 8.58 (s, 1H), 8.21 (d, 2H), 7.99 (d, 1H), 7.94 (d, 1H), 7.76 (d, 1H), 7.61 (m, 2H), 7.31 (t, 1H), 7.14 (d, 1H), 7.06 (t, 1H), 3.83 (s, 3H). MS: m/e 345.1 (M+H+).

Workup

  1. washThe sides of the flask were rinsed with additional acetic acid (3 mL)
  2. customto precipitate out of solution
  3. stirringThe reaction was stirred for an additional hour at ambient temperature
  4. filtrationThe precipitate was filtered
  5. washrinsed well with acetic acid and diethyl ether

Sources & evidence

ORD record
ord-4011d71c1b8a42239b68804051eda8aa
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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