Triphenylphosphine → HCID 86686103, compound

HRID 882196Notes

Reaction equation

HRID 882196 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)=[CH:12][C:7]=2[N:6]([CH3:20])[C:5]1=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:43][C:44]1[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=1[CH2:46]O.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:46][C:45]4[CH:48]=[CH:49][CH:50]=[CH:51][C:44]=4[F:43])[CH:14]=3)=[CH:12][C:7]=2[N:6]([CH3:20])[C:5]1=[O:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 679692-Fluorobenzylic alcoholHCID 97268Di-tert-butyl azodicarboxylateHCID 56656122HCID 56656122, compound

Product 1

HCID 86686103HCID 86686103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An orange solution of 1-(2,2-dimethylpropyl)-5-(3-hydroxyphenyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-179, 70 mg, 0.23 mmol) in Dichloromethane (10 ml) was treated with polymer bound-Triphenylphosphine (177 mg, 0.68 mmol, 3.0 eq) and the 2-Fluorobenzyl alcohol (56.9 mg, 0.45 mmol, 2.0 eq). The mixture was charged, in portions, with Di-tert-butyl azodicarboxylate (104 mg, 0.45 mmol, 2.0 eq) and the resulting maroon-orange solution was stirred at 23 deg C. for 1 h. The reaction mixture was filtered through a frit and the filtrate was purified via flash column chromatography (SiO2: 100% Hex to 75:25% Hex:EtOAc) to afford the title compound, 1-(2,2-dimethylpropyl)-5-{3-[(2-fluorobenzyl)oxy]phenyl}-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (3-1), as an orange oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (t, 1H, J=7.0 Hz), 7.38-7.26 (m, 3H), 7.22-7.15 (m, 3H), 7.13-7.06 (m, 3H), 6.97 (d, 1H, J=7.1 Hz), 5.21 (s, 2H), 3.68 (s, 2H), 3.47 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C26H27FN2O2 (M+H) 419.2, found 419.3.

Workup

  1. filtrationThe reaction mixture was filtered through a frit
  2. customthe filtrate was purified via flash column chromatography (SiO2: 100% Hex to 75:25% Hex:EtOAc)

Sources & evidence

ORD record
ord-67d258e11bc94dc9b00226a376dd204c
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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