2-Fluoro-4-iodoaniline → HCID 25070529, compound

HRID 559059Notes

Reaction equation

HRID 559059 reaction equation
[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:11]=1[NH2:12].[CH:18]1([N:21]2[C:30]3[C:25](=[C:26](F)[C:27]([F:32])=[CH:28][C:29]=3[F:31])[C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22]2)[CH2:20][CH2:19]1>C1COCC1.CN1C(=O)CCC1>[CH:18]1([N:21]2[C:30]3[C:25](=[C:26]([NH:12][C:11]4[CH:13]=[CH:14][C:15]([I:17])=[CH:16][C:10]=4[F:9])[C:27]([F:32])=[CH:28][C:29]=3[F:31])[C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22]2)[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 1856942-Fluoro-4-iodoanilineHCID 2724682Lithium diisopropylamideHCID 19807252HCID 19807252, compound

Product 1

HCID 25070529HCID 25070529, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

LDA (2N solution in heptane/tetrahydrofuran/ethylbenzene, 0.39 mL, 0.77 mmol) was added dropwise to a stirred solution of 2-fluoro-4-iodoaniline (165 mg, 0.70 mmol) in THF (1.2 mL) at −78° C. After 15 minutes, a solution of example 1d (100 mg, 0.35 mmol) in NMP (1.8 mL) was then added at −78° C. The reaction mixture was allowed to warm to room temperature and stirred for 25 h. Purification by preparative HPLC mass triggered gave 7.6 mg (5%) of the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 13.92 (s, 1H), 10.39 (s, 1H), 8.71 (s, 1H), 8.11 (t, 1H, J=11.2 Hz), 7.65 (d, 1H, J=10.4 Hz), 7.44 (d, 1H, J=8.4 Hz), 6.74-6.79 (m, 1H), 4.12-4.19 (m, 1H), 1.15-1.22 (m, 4H). MS (ES) [m+H] calc'd for C19H12F3IN2O3, 501; found 501.

Workup

  1. customPurification by preparative HPLC mass

Sources & evidence

ORD record
ord-df87290141204d7bb5eda3ccaa86635d
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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