HCID 21191334, compound → HCID 10488759, compound

HRID 1069112Notes

Reaction equation

HRID 1069112 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[C:10]([CH2:20][Cl:21])=[CH:9]1)=O)(C)(C)C>Cl>[Cl:21][CH2:20][CH:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[NH:8][CH2:9]1

Participants

3

Reactant 1

HCID 21191334HCID 21191334, compound

Product 1

HCID 10488759HCID 10488759, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-(tert-Butyloxycarbonyl)-3-chloromethyl-6-nitroindole (156 mg, 0.50 mmol) was stirred in HCl-saturated dioxane (5 mL) at 20° C. for 2 h, and the mixture was then evaporated to dryness under high vacuum below 25° C. to give crude 3-chloromethyl-6-nitroindoline (6). Acid 11 (135 mg, 0.50 mmol), EDCI.HCl (240 mg, 1.25 mmol) and DMA (1.5 mL) were then added in sequential fashion and the mixture was stirred at 20° C. for 2 h. Dilution with water provided the crude product which was recrystallised twice from EtOAc to give 1-[(E)-3-(1-methylpyrrole-2-carboxamido)-cinnamoyl]-3-chloromethyl-6-nitroindole (12) (166 mg, 72%), mp 215° C. 1H NMR [(CD3)2SO] δ9.86 (s, 1 H, NH), 8.97 (s, 1 H, H-7), 8.03-7.96 (m, 1 H, H-5), 8.00 (s, 1 H, H-2′), 7.80 (d, J=8.0 Hz, 1 H, H-4′), 7.70 (d, J=8.3 Hz, 1 H, H-4), 7.69 (d, J=15.4 Hz, 1 H, PhCH═CH), 7.54 (d, J=7.4 Hz, 1 H, H-6′), 7.41 (t, J=7.9 Hz, 1 H, H-5′), 7.11 (d, J=15.4 Hz, 1 H, PhCH═CH), 7.1-7.04 (m, 2 H, H-pyrrole), 6.12 (t, J=3.1 Hz, 1 H, H-pyrrole), 4.66 (t, J=10.0 Hz, 1 H, H-2), 4.34 (dd, J=10.6, 5.1 Hz, 1 H, H-2), 4.15-3.99 (m, 3 H, H-3, CH2Cl ), 3.90 (s, 3 H, NCH3).

Workup

  1. customthe mixture was then evaporated to dryness under high vacuum below 25° C.

Sources & evidence

ORD record
ord-ba6f27ab674542d98d62fedd42f0aaea
Source dataset
uspto-grants-2001_06
Patent number
US06251933B1

Reaction notes

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