3-Chloro-2-fluoroaniline → HCID 57618493, compound

HRID 1690696Notes

Reaction equation

HRID 1690696 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.Cl.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:30]N)[CH:25]=2)=[CH:20][C:19]=1[CH3:32].CC1C=C(B(O)O)C=CC=1[F:40].ClC1C(F)=C(C=CC=1)N>>[F:40][C:25]1[C:26]2[NH:30][C:2]3[C:10]4[C:5]([CH2:4][C:3]=3[C:27]=2[CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([F:17])=[C:19]([CH3:32])[CH:20]=1)=[CH:6][C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=4

Participants

5

Reactant 4

HCID 750143-Chloro-2-fluoroanilineHCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 22181912HCID 22181912, compoundHCID 66904603HCID 66904603, compound

Product 1

HCID 57618493HCID 57618493, compoundYield 29%

Procedure

The title material is prepared in 29% yield by reacting N-(1-Oxo-indan-5-yl)-methanesulfonamide and (4′-Fluoro-3′-methyl-biphenyl-3-yl)-hydrazine hydrochloride (prepared as in example 70, steps 1 and 2 except using 3-methyl-4-fluorophenylboronic acid and 3-chloro-2-fluoroaniline as the coupling partners) in an analogous manner to example 1, step 3 except that purification is accomplished by reverse phase UV triggered HPLC: 1H NMR (400 MHz, d6-DMSO) δ 12.08 (s, 1H), 9.75 (s, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.55-7.50 (m, 1H), 7.48-7.40 (m, 3H), 7.28-7.22 (m, 2H), 7.14-7.09 (m, 1H), 3.74 (s, 2H), 3.01 (s, 3H), 2.34-2.31 (m, 3H); LC/MS calculated for [M+H]+ C23H18F2N2O2S: 425.1, found: 425.1.

Workup

  1. customprepared as in example 70, steps 1 and 2
  2. customexcept that purification

Sources & evidence

ORD record
ord-c9d0cf4414c34eb396e445ffc1163221
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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