3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline → HCID 67347154, compound

HRID 1676260Notes

Reaction equation

HRID 1676260 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][S:7](=[O:10])[CH2:6][CH2:5]1)[C:2]#[CH:3].[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]>>[NH2:15][C:14]1[CH:16]=[CH:17][C:18]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[CH:26]=[C:27]([C:3]#[C:2][CH2:1][N:4]4[CH2:9][CH2:8][S:7](=[O:10])[CH2:6][CH2:5]4)[S:28][C:21]=23)=[C:12]([F:11])[CH:13]=1

Participants

3

Reactant 2

HCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineHCID 61555475HCID 61555475, compound

Product 1

HCID 67347154HCID 67347154, compoundYield 83.3%

Conditions

Temperature
50 °C

Procedure

Prepared from N-propargyl S-oxo-4-thiapiperidine (30.5 mg, 0.194 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 50 mg, 0.13 mmol) according to the procedure described for Example 6, Step B, except the reaction was heated at 50° C. for 7 hours. The crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]. The product was obtained as a waxy solid (45 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J=6 Hz, 1H), 7.61 (s, 1H), 7.03 (m, 1H), 6.53 (m, 2H), 6.47 (m, 1H), 3.89 (br s, 2H), 3.64 (s, 2H), 3.25 (m, 2H), 2.92 (m, 6H).

Workup

  1. customThe crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]

Sources & evidence

ORD record
ord-e50ea1c61fe54471a6377a98ca41eebb
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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