(But-3-yn-1-yl)diethylamine → 4-(2-(4-(Diethylamino)but-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 1676249Notes

Reaction equation

HRID 1676249 reaction equation
[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][C:6]#[CH:7])[CH3:2].[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]2[CH:25]=[C:26](I)[S:27][C:20]=12)[NH2:14]>>[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][C:6]#[C:7][C:26]1[S:27][C:20]2[C:21](=[N:22][CH:23]=[CH:24][C:19]=2[O:18][C:17]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=2[F:10])[CH:25]=1)[CH3:2]

Participants

3

Reactant 2

HCID 12225176(But-3-yn-1-yl)diethylamineHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 673486374-(2-(4-(Diethylamino)but-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 6%

Conditions

Temperature
50 °C

Procedure

Prepared from N,N-diethylbut-3-yn-1-amine (30 mg, 1.04 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 200 mg, 0.518 mmol) according to the procedure described for Example 6, Step B, except the reaction was heated to 50° C. for 7 hours. The crude was purified by preparative TLC (10% MeOH/EtOAc). The product was obtained as a waxy solid (12 mg, 6%). 1H NMR (400 MHz, CDCl3) δ 8.46 (d, J=6 Hz, 1H), 7.52 (s, 1H), 7.03 (m, 1H), 6.52 (m, 3H), 3.85 (s, 2H), 2.88 (m, 2H), 2.67 (m, 6H), 1.12 (m, 6H).

Workup

  1. customThe crude was purified by preparative TLC (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-f57948481a904924affe5e9e2d5a8541
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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