Triphenylphosphine → HCID 57937553, compound

HRID 1435129Notes

Reaction equation

HRID 1435129 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)=[CH:15][C:10]=3[N:9]=[CH:8]2)[S:4][C:3]=1[C:22]([O:24][CH3:25])=[O:23].O[CH:27]([C:29]1[CH:30]=[C:31]([O:35][CH:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]2)[CH:32]=[CH:33][CH:34]=1)[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH3:25][O:24][C:22]([C:3]1[S:4][C:5]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:6][C:2]=1[O:1][CH:27]([C:29]1[CH:30]=[C:31]([O:35][CH:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[CH2:38][CH2:37]2)[CH:32]=[CH:33][CH:34]=1)[CH3:28])=[O:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57937504HCID 57937504, compoundHCID 57937534HCID 57937534, compound

Product 1

HCID 57937553HCID 57937553, compoundYield 249.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-hydroxy-5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylate (0.300 g, 0.847 mmol), (+/−)-1,1-dimethylethyl 4-{[3-(1-hydroxyethyl)phenyl]oxy}-1-piperidinecarboxylate (0.285 mmol), and triphenylphosphine (0.667 g, 2.54 mmol) were dissolved in 25 mL of DCM with stirring. Diisopropyl azodicarboxylate was added slowly dropwise via syringe. The reaction was stirred overnight, and the mixture was adsorbed onto silica gel. Purification by flash chromatography afforded 0.467 g (84%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.68 (s, 1H), 8.17 (s, 1H), 7.94 (s, 1H), 7.90 (s, 1H), 7.56 (s, 2H), 7.48 (s, 1H), 7.26 (dd, J=8.1, 7.9 Hz, 1H), 7.08 (m, 1H), 7.01 (d, J=7.9 Hz, 1H), 6.87 (dd, J=8.1, 2.2 Hz, 1H), 5.69 (q, J=6.0 Hz, 1H), 4.50 (m, 1H), 3.84 (s, 3H), 3.78 (s, 3H), 3.65-3.56 (m, 2H), 3.18-3.05 (m, 2H), 1.91-1.78 (m, 2H), 1.58 (d, J=6.2 Hz, 3H), 1.53-1.40 (m, 2H), 1.35 (s, 9H).

Workup

  1. stirringThe reaction was stirred overnight
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c638c099bfa0477bb0f2821be3cd058e
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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