Triphenylphosphine → HCID 59497610, compound

HRID 1747381Notes

Reaction equation

HRID 1747381 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:33][N:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[CH2:43]O)[CH:36]=[C:35]1[CH3:45].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:33][N:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[CH2:43][N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]2=[O:13])[CH:36]=[C:35]1[CH3:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 59497574HCID 59497574, compound

Product 1

HCID 59497610HCID 59497610, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-isopropenylbenzimidazolone (220 mg, 1.3 mmol) in dry THF (10 mL) are added triphenylphosphine (397 mg, 1.5 mmol) and (1,2-Dimethyl-1H-indol-7-yl)-methanol (220 mg, 1.3 mmol). Then diisopropyl azodicarboxylate (0.31 mL, 1.5 mmol) is added drop wise into the above solution at room temperature. The mixture is stirred for 16 hrs and then the solvent is removed under vacuum. The residue is purified by flash column chromatography using 10-30% EtOAc in hexanes to give 200 mg (48%) of 1-(1,2-dimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-1,3-dihydro-benzimidazol-2-one.

Workup

  1. customthe solvent is removed under vacuum
  2. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-6adcc191ecbc431dbf031f497e9705f5
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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