Hydrochloric Acid → 3-(6-Hydroxymethyl-2-methyl-imidazo[1,2-a]pyridin-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

HRID 216674Notes

Reaction equation

HRID 216674 reaction equation
Cl.C([SiH2][O:7][C:8](C1C=CC=CC=1)(C1C=CC=CC=1)[C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:19]3[C:20](=[O:34])[NH:21][C:22](=[O:33])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[C:16]([CH3:18])[N:17]=2)[CH:14]=1)(C)(C)C>>[OH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:19]3[C:20](=[O:34])[NH:21][C:22](=[O:33])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[C:16]([CH3:18])[N:17]=2)[CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 1317297543-[6-[tert-butylsilyloxy(diphenyl)methyl]-2-methylimidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione

Product 1

HCID 591920313-(6-Hydroxymethyl-2-methyl-imidazo[1,2-a]pyridin-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dioneYield 83.3%

Conditions

Temperature
45 °C

Procedure

A 4 M aqueous solution of hydrochloric acid (5.0 ml) is added to 3-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione (180 mg, 0.29 mmol). The reaction mixture is stirred for 24 hours at 45° C. After removal of volatiles in vacuo, purification via flash chromatography (CH2Cl2/MeOH 95:5) affords the title compound (90 mg, 82%). 1H NMR (400 MHz, d6-DMSO): δ=11.94 (s, 1H), 11.08 (s, 1H), 8.05 (s, 1H), 7.91 (s, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.13 (dd, J=9.0/1.8 Hz, 1H), 6.92 (dt, J=7.8/1.0 Hz, 1H), 6.46 (dt, J=7.6/1.0 Hz, 1H), 5.90 (d, J=8.0 Hz, 1H), 5.14 (t, J=5.4 Hz, 1H), 4.25 (t, J=4.7 Hz, 2H), 1.84 (s, 3H). (ES+): 373 (M+H)+.

Workup

  1. customAfter removal of volatiles
  2. customin vacuo, purification via flash chromatography (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-69de1427166c40339e243c652cb1c421
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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