Methanol → Methyl 3-chloro-1H-pyrrole-2-carboxylate

HRID 2170151Notes

Reaction equation

C[C:2]1[CH2:6][CH2:5][CH2:4][N:3]=1.C1C(=O)N([Cl:14])C(=O)C1.[CH3:15][O-:16].[Na+].[CH3:18][OH:19]>>[Cl:14][C:6]1[CH:5]=[CH:4][NH:3][C:2]=1[C:15]([O:19][CH3:18])=[O:16]

Participants

Reactant 4

HCID 887Methanol

HCID 31398Chlorosuccinimide

HCID 701032-Methyl-1-pyrroline

HCID 10942334Sodium Methoxide

Product 1

HCID 5324605Methyl 3-chloro-1H-pyrrole-2-carboxylateYield 94%

Procedure

The commercially available methyl 3-chloro-1H-pyrrole-2-carboxylate (1.50 g, 94.0%, yellow solid) was synthesized according to Fang et al., J. Med. Chem., 53:7967-7978 (2010) using 2-methyl-1-pyrroline (0.831 g, 10.0 mmol, commercial), NCS (10.7 g, 80.0 mmol) and NaOMe in MeOH (3M, 20 mL, 60.0 mmol). LCMS Condition B-41: retention time 1.71 min, [M+1]=160.10. 1H NMR (400 MHz, CDCl3) δ 3.90 (s, 3H), 6.25 (t, J=3.0 Hz, 1H), 6.86 (t, J=3.0 Hz, 1H), 9.17 (br s, 1H).

Sources & evidence

ORD record: ord-15b9ac65784b4b02ba742650b24c62be
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050345B2

Reaction notes

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