3-Chloro-2-fluoroaniline → HCID 16046861, compound

HRID 1690691Notes

Reaction equation

HRID 1690691 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[C:4](=O)[CH2:3]1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20](C2C=CC=C(NN)C=2)=[CH:19][C:18]=1[CH3:31].CC1C=C(B(O)[OH:41])C=CC=1F.Cl[C:44]1[C:45]([F:51])=[C:46]([CH:48]=[CH:49][CH:50]=1)[NH2:47]>>[F:51][C:45]1[C:46]2[NH:47][C:4]3[C:5]4[C:10]([C:2]([CH3:14])([CH3:1])[C:3]=3[C:48]=2[CH:49]=[CH:50][C:44]=1[C:20]1[CH:21]=[CH:22][C:17]([F:16])=[C:18]([CH3:31])[CH:19]=1)=[CH:9][C:8]([C:11]([NH2:12])=[O:41])=[CH:7][CH:6]=4

Participants

5

Reactant 4

HCID 750143-Chloro-2-fluoroanilineHCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 14896361HCID 14896361, compoundHCID 66904603HCID 66904603, compound

Product 1

HCID 16046861HCID 16046861, compound

Procedure

Steps 6 and 7: A sample of 3,3-dimethyl-1-oxo-indan-5-carbonitrile 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) are reacted together as in example 1, step 3. The crude product is then subjected to hydrolysis as in example 19, step 3 to afford 6-fluoro-7-(4-fluoro-3-methyl-phenyl)-10,10-dimethyl-5,10-dihydro-indeno[1,2-b]indole-2-carboxylic acid amide as a light yellow solid: 1H NMR (400 MHz, acetone-d6) δ 11.18 (s, 1H), 8.14 (s, 1H), 7.95 (dd, 1H, J=1.2, 7.6 Hz), 7.68 (d, 1H, J=8 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.54 (dd, 1H, J=0.8, 7.6 Hz), 7.46-7.45 (m, 2H), 7.20-7.25 (m, 2H), 6.65-6.50 (br, 2H), 225 (d, 3H, J=1.6 Hz), 1.66 (s, 6H), ESMS 77/z 403.2 (M+H+).

Workup

  1. customare reacted together as in example 1, step 3

Sources & evidence

ORD record
ord-39ab8ebafcfe44b6ab34b9ca36430239
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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