Imidazole → HCID 22270368, compound

HRID 30352Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)(O)C)=C[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:39]1[CH:43]=[CH:42]N=C1.CCOC(/[N:49]=[N:50]/C(OCC)=O)=O.C(Cl)[Cl:57]>>[N:39]([CH:43]([CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:9][C:8]1[CH:3]=[CH:2][C:7]([Cl:57])=[CH:6][CH:5]=1)[CH3:42])=[N+:49]=[N-:50]

Participants

Reactant 5

HCID 795Imidazole

HCID 6344Dichloromethane

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 222705264-(4-Chlorophenyl)-2-(3-fluorophenyl)-2-butanol

Product 1

HCID 22270368HCID 22270368, compound

Procedure

To a mixture of 4-(4-chlorophenyl)-2-(3-fluorophenyl)-2-butanol (Step 3, 0.65 g, 2.3 mmol), triphenylphosphine (1.2 g, 4.7 mmol), imidazole (0.32 g, 4.7 mmol) and zinc azide dipyridine complex (Viaud, M. C.; Rollin, P. Synthesis 1990, 130) (0.72 g, 2.3 mmol) in 10 mL of methylene chloride was added diethylazodicarboxylate (0.73 mL, 4.7 mmol) at 0° C. After stirring at room temperature for 30 min, the resulting mixture was concentrated with silica gel (20 g) and loaded onto a silica gel column, which was eluted with 2% ether in hexane to 2% ammonia in methanol (2 M) in 2% ether/hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.25-6.85 (m, 8H), 3.76 (m, 1H), 3.33 (m, 11H), 2.92 (m, 2H), 1.15 (d, 3H).

Workup

concentrationthe resulting mixture was concentrated with silica gel (20 g)
washwas eluted with 2% ether in hexane to 2% ammonia in methanol (2 M) in 2% ether/hexane

Sources & evidence

ORD record: ord-2b18f4f7a1724f8685beb28bdc7ea1ba
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423067B2

Reaction notes

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