Iodine → HCID 56598012, compound

HRID 238563Notes

Reaction equation

HRID 238563 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C@H:31]([C:45]([OH:48])([CH3:47])[CH3:46])[C:32]([NH:34][NH:35][C:36](=[O:44])[C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)=O)=[C:26]([CH3:49])[C:25]=1[C:50]([F:53])([F:52])[F:51])#[N:23]>C(Cl)Cl.C1COCC1>[F:43][C:40]1[CH:39]=[CH:38][C:37]([C:36]2[O:44][C:32]([C@H:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[C:25]([C:50]([F:52])([F:51])[F:53])[C:26]=3[CH3:49])[C:45]([OH:48])([CH3:47])[CH3:46])=[N:34][N:35]=2)=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 807IodineHCID 11776TriphenylphosphineHCID 66625420(R)-N'-(2-(4-cyano-2-methyl-3-(trifluoromethyl)phenylamino)-3-hydroxy-3-methylbutanoyl)-4-fluorobenzohydrazide

Product 1

HCID 56598012HCID 56598012, compoundYield 123.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (766 mg, 2.92 mmol) was dissolved in DCM (100 mL) followed by addition of I2 (741 mg, 2.92 mmol) and TEA (0.81 mL, 5.84 mmol) at 0° C. (R)—N′-(2-(4-cyano-2-methyl-3-(trifluoromethyl)phenylamino)-3-hydroxy-3-methylbutanoyl)-4-fluorobenzohydrazide (660 mg, 1.46 mmol) in DCM (20 mL) and THF (10 mL) was added to the pre-cooled solution mixture of PPh3/I2/TEA system and stirred for 30 min. The reaction mixture was then concentrated to furnish a yellow solid (781 mg). The crude material was chromatographed with EtOAc:Hexanes (2:1) to furnish the title compound as a white solid (361 mg, 57%). 1H NMR (500 MHz, Acetone d6, δ in ppm): 7.97-7.94 (m, 2H), 7.49 (d, J=9 Hz, 1H), 7.19-7.14 (m, 2H), 6.81 (d, J=9 Hz, 1H), 5.55 (d, J=9 Hz, 1H), 4.72 (d, J=9 Hz, 1H), 2.35 (s, 3H), 1.50 (s, 3H) and 1.35.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-30f67d1d91a94b0d8dd043b73fbe67c8
Source dataset
uspto-grants-2014_02
Patent number
US08642632B2

Reaction notes

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