Water → 1-(4-Methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 40720

Reaction equation

[H-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:6].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.O>CN(C=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:13]2[C:10]3=[N:11][CH:12]=[C:7]([C:5]([OH:4])=[O:6])[CH:8]=[C:9]3[CH:15]=[CH:14]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred cooled 0° C. suspension of NaH (272 mg, 6.81 mmol) in DMF (23 mL) was added 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (400 mg, 2.27 mmol). After 5 min, PMBBr (548 mg, 2.72 mmol) and KI (377 mg, 2.27 mmol) were added and the reaction mixture was allowed to warm to room temperature and stirring was continued overnight. The following day, water was added to quench the remaining Nail and the aqueous mixture was washed with EtOAc, which was discarded. The aqueous phase was collected and carefully acidified (pH ˜3) before extraction with EtOAc. The combined organics were dried and evaporated to afford 1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (160 mg, 0.57 mmol, 25% yield). ES MS (M+H+)=283.

Workup

temperatureto warm to room temperature
waitwas continued overnight
customto quench the remaining Nail
washthe aqueous mixture was washed with EtOAc, which
customThe aqueous phase was collected
extractionbefore extraction with EtOAc
customThe combined organics were dried
customevaporated

Sources & evidence

ORD record: ord-7decd16c2ab94af9ac129939d6ac8506
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530483B2

Linked notes

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