3-Chloro-4-fluoroaniline → HCID 57377420, compound

HRID 1529827Notes

Reaction equation

[NH2:1][C:2]1[Se:3][C:4]([CH3:15])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].C[N:17]([CH:19](OC)OC)C.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[F:32])N.[K+].[Br-]>C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([NH:8][C:7]2[C:6]3[C:5]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)=[C:4]([CH3:15])[Se:3][C:2]=3[N:1]=[CH:19][N:17]=2)[CH:29]=[CH:30][C:31]=1[F:32]

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of 2-amino-5-methyl-4-phenylselenophene-3-carbonitrile (1.0 g, 3.81 mmol) in toluene (30 mL) was added sequentially acetic acid (0.2 mL) and DMF-DMA (1.14 mL, 8.01 mol). The reaction mixture was stirred at 105° C. for 2 h and treated with 3-chloro-4-fluoroaniline (670 mg, 4.57 mmol) as described in example 12, gave the product as an off-white color solid, mp 166-168° C. IR (KBr) νmax 3397, 3020, 1614, 1563, 1498, 1433, 1263, 1196, 1145, 967, 904, 868, 774 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.51 (1H, s), 7.59-7.62 (3H, m), 7.55 (1H, dd, J=6.4, 2.8 Hz), 7.42-7.45 (2H, m), 6.94 (1H, t, J=8.8 Hz), 6.76-6.96 (1H, m), 6.45 (1H, br s), 2.40 (3H, s); 13C NMR (100 MHz, CDCl3): δ 170.2, 154.4, 154.0 (d, J=244.0 Hz), 152.0, 139.4, 136.4 (d, J=3.0 Hz), 131.9, 130.0, 130.0, 129.6, 129.2, 121.8, 120.8 (d, J=18.0 Hz), 119.3 (d, J=7.0 Hz), 118.9, 116.3 (d, J=22.0 Hz), 16.3; LC-MS (positive ion mode): m/z 416, 418, 420 (M+H)+.

Workup

customgave the product as an off-white color solid, mp 166-168° C

Sources & evidence

ORD record: ord-1dcab3eb113a4276944e27069f2b2cdb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090633B2

Reaction notes

Loading…