Hydrochloric Acid → (S)-methyl 6-chloro-5-(3-methoxy-4-(pyrrolidin-2-ylmethoxy)phenyl)-1H-indole-3-carboxylate

HRID 338357Notes

Reaction equation

HRID 338357 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][C:29]=2[Cl:30])[NH:26][CH:25]=[C:24]3[C:31]([O:33][CH3:34])=[O:32])=[CH:17][C:16]=1[O:35][CH3:36])=O)(C)(C)C.Cl>ClCCl>[Cl:30][C:29]1[CH:28]=[C:27]2[C:23]([C:24]([C:31]([O:33][CH3:34])=[O:32])=[CH:25][NH:26]2)=[CH:22][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[C:16]([O:35][CH3:36])[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86698696(S)-methyl 5-(4-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxy)-3-methoxyphenyl)-6-chloro-1H-indole-3-carboxylate

Product 1

HCID 86698697(S)-methyl 6-chloro-5-(3-methoxy-4-(pyrrolidin-2-ylmethoxy)phenyl)-1H-indole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 5-(4-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methoxy)-3-methoxyphenyl)-6-chloro-1H-indole-3-carboxylate (25.8 mg, 0.050 mmol) in dichloromethane (0.5 mL) was added hydrogen chloride (4M solution in dioxane, 0.075 mL, 0.30 mmol). After 2 h, the solution was concentrated in vacuo to provide the title compound as the hydrochloride salt contaminated with neopentyl glycol. MS (ES+) 415.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 8.80 (br. s, 1H), 8.17 (d, 1H), 7.94 (s, 1H), 7.65 (s, 1H), 7.11 (d, 1H), 7.06 (d, 1H), 6.96 (dd, 1H), 4.34-4.26 (m, 2H), 4.15 (dd, 1H), 4.01-3.92 (m, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.29-3.19 (m, 2H), 2.21-2.10 (m, 1H), 2.08-1.86 (m, 2H), 1.83-1.72 (m, 1H).

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-8dc91582b57946a79d81725e2a278597
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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