Triphenylphosphine → 1-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-5-methyl-1,3-dihydro-benzimidazol-2-one

HRID 1747312Notes

Reaction equation

HRID 1747312 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:14])([CH3:3])=[CH2:2].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([CH2:25]O)[CH:24]=1)[N:21]([CH3:27])[C:20]([CH3:28])=[C:19]2[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([CH2:25][N:6]3[C:7]4[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=4[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]3=[O:14])[CH:24]=1)[N:21]([CH3:27])[C:20]([CH3:28])=[C:19]2[CH3:29]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 41843121-Isopropenyl-6-methyl-1,3-dihydro-benzimidazol-2-oneHCID 5363146Diisopropyl azodicarboxylateHCID 59497324(5-Chloro-1,2,3-trimethyl-1H-indol-7-yl)-methanol

Product 1

HCID 594976701-(5-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-3-isopropenyl-5-methyl-1,3-dihydro-benzimidazol-2-oneYield 56.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Isopropenyl-6-methyl-1,3-dihydro-benzimidazol-2-one (50 mg, 0.27 mmol) and (5-Chloro-1,2,3-trimethyl-1H-indol-7-yl)-methanol (60 mg, 0.27 mmol), triphenylphosphine (84 mg, 0.32 mmol) in THF (2 mL) was added dropwise DIAD (0.06 mL, 0.32 mmol). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 60 mg of the desired product as a brownish oil. LCMS (ESMS): m/z 394.28 (M+H+).

Workup

  1. washwashed with water (×2)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-84714b4538a14888aff50f37dbd688ea
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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