Sodium Carbonate → HCID 178498259, compound

HRID 392206Notes

Reaction equation

HRID 392206 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[NH:8][C:9]3[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[C:12]([O:20][CH3:21])[C:10]=3[N:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C(B(CC)[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)C>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][O:20][C:12]1[C:10]2[N:11]=[C:7]([CH2:6][C:5]3[CH:22]=[CH:23][C:2]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)=[CH:3][CH:4]=3)[NH:8][C:9]=2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 178498258HCID 178498258, compound

Product 1

HCID 178498259HCID 178498259, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of methyl 2-(4-bromobenzyl)-7-methoxy-3H-benzimidazole-4-carboxylate [0.268 g, Reference Example 3(1)] in toluene (8 ml) was treated with tetrakis(triphenylphosphine) palladium (0) (0.266 g), aqueous sodium carbonate solution (0.5 ml, 2M) and diethyl (3-pyridyl)borane (0.085 g). The mixture was heated at reflux for 12 hours then cooled to room temperature. Aqueous work-up and subjected to flash chromatography on silica to give the title compound (0.128 g). NMR {(CD3)2SO}: δ 3.90(s, 3H), 4.10(s, 3H), 4.40(s, 2H), 6.70(d, 1H), 7.45(d, 3H), 7.60(d, 3H), 7.90 (dd, 1H), 8.60(d, 1H), 8.85(d, 1H), 10.10(s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 hours

Sources & evidence

ORD record
ord-bfd74601f32c466197f8a9c2a368c4d7
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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