Sodium hydride → methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylate

HRID 1435440Notes

Reaction equation

HRID 1435440 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[H-].[Na+].[C:12]([C:16]1[N:20]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:19]2[CH:28]=[CH:29][C:30]([S:32](Cl)(=[O:34])=[O:33])=[CH:31][C:18]=2[N:17]=1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([C:16]1[N:20]([CH2:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:19]2[CH:28]=[CH:29][C:30]([S:32]([N:1]3[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]3)(=[O:33])=[O:34])=[CH:31][C:18]=2[N:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12361759methyl 1H-pyrrole-3-carboxylateHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 23660111methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure in Example 29, using methyl 1H-pyrrole-3-carboxylate (0.16 g, 1.3 mmol) (see following step B for preparation), sodium hydride (0.18 g, 60%, 4.5 mmol) and 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (0.48 g, 1.3 mmol) in THF (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.16 g (27%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.46-1.54 (m, 4 H), 1.56 (s, 9 H), 2.15-2.32 (m, 1 H), 3.25-3.37 (m, 2 H), 3.79 (s, 3 H), 3.93-4.03 (m, 2 H), 4.22 (d, J=7.42 Hz, 2 H), 6.62 (dd, J=3.32, 1.56 Hz, 1 H), 7.15 (dd, J=3.32, 2.34 Hz, 1 H), 7.42 (d, J=8.79 Hz, 1 H), 7.74-7.81 (m, 2 H), 8.33 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=459.8; Anal. Calcd for C23H29N3O5S+0.10 EtOAc+0.30H2O (474.98): C, 59.43; H, 6.45; N, 8.85. Found: C, 59.34; H, 6.60; N, 8.84.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-42876a0af0514481ad40c629e8d3f3bd
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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