Triphenylphosphine → 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747364Notes

Reaction equation

HRID 1747364 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[CH2:31]O)[C:24]([CH3:33])=[C:23]1[CH3:34].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:31][C:29]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:30]=2[N:22]([CH3:21])[C:23]([CH3:34])=[C:24]3[CH3:33])[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497596HCID 59497596, compound

Product 1

HCID 594972503-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl esterYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (100 mg, 0.36 mmol) in THF (10 mL) were added (1,2,3-Trimethyl-1H-indol-7-yl)-methanol (103 mg, 0.54 mmol), DIAD (diisoproyl azo-dicarboxylate) (0.14 mL, 0.7 mmol) and triphenylphosphine (95 mg, 0.36 mmol) at room temperature. The solution was stirred at the same temperatrue for 12 hours. The solution was filtered and the filtrate was concentrated. The residue was purified by combFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 3-[2-Oxo-3-(1,2,3-trimethyl-1H-indol-7-ylmethyl)-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (80 mg, 49%) as a white foam.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by combFlash with 10% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-bdec2d67ad4549ec9740231c4437a360
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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