N,N-diethyl-2-methylbut-3-yn-2-amine → 4-(2-(3-(Diethylamino)-3-methylbut-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine
Reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[C:4]([CH3:8])([C:6]#[CH:7])[CH3:5])[CH3:2].[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27](I)[S:28][C:21]=12)[NH2:15]>>[CH2:1]([N:3]([CH2:9][CH3:10])[C:4]([CH3:8])([CH3:5])[C:6]#[C:7][C:27]1[S:28][C:21]2[C:22](=[N:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=2[F:11])[CH:26]=1)[CH3:2]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
Prepared from N,N-diethyl-2-methylbut-3-yn-2-amine (21 mg, 0.15 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 39 mg, 0.10 mmol) using the procedure described for Example 6, Step B, except the reaction was heated to 50° C. for 24 hours. The crude was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (13 mg, 31%). 1H NMR (400 MHz, CDCl3) δ 8.47 (m, 1H), 7.51 (s, 1H), 7.02 (m, 1H), 6.49 (m, 3H), 3.85 (s, 2H), 2.76 (m, 4H), 1.52 (s, 6H), 1.14 (m, 6H).
Workup
- customThe crude was purified by preparative TLC (10% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-208908b2ab7c4890a27ded263d57b3bd
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003662B2
Reaction notes
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