Pyridine → HCID 71089555, 화합물

HRID 710102노트

반응식

HRID 710102 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].N1C=CC=CC=1.[F:16][CH:17]([F:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22](=[O:23])[C:21]2[CH:20]=[CH:19][C:18]([CH:17]([F:16])[F:27])=[CH:26][CH:25]=2)=[C:3]([OH:9])[CH:4]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 143206052-Amino-5-bromophenolHCID 86676951HCID 86676951, 화합물

생성물 1

HCID 71089555HCID 71089555, 화합물수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

4-(difluoromethyl)benzoic acid (0.7 g, 4 mmol) dissolved in DCM (20 ml), cooled to 0° C. and added oxalyl chloride (0.8 g, 6.1 mmol). Catalytic amount of DMF was added to this mixture and stirred at rt for 30 mins. After 30 mins, DCM removed on rotavapour and co-distilled the residue two times with DCM to obtain 4-(difluoromethyl)benzoyl chloride quantitatively. 2-Amino-5-bromophenol (0.64 g, 3.4 mmol) dissolved in DCM (20 ml) and added Pyridine (0.32 ml, 4.1 mmol) under nitrogen atmosphere. This mixture stirred at rt for 30 mins and added 4-(difluoromethyl)benzoyl chloride (0.77 g, 4.1 mmol). After continuing stirring at rt for 15 mins, reaction mass diluted with water and extracted with DCM. DCM layer washed with aq. NaHCO3 and DCM removed on rotavapour to obtain the solid. Solid was triturated with Et2O and Petether mixture (4:1) to obtain the titled compound (0.5 g) as a yellow solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.27 (s, 1H), 9.62 (s, 1H), 8.07 (d, J 8.2, 2H), 7.71 (d, J 8.2, 2H), 7.61 (d, J 8.5, 1H), 7.12 (t, J 55.7, 1H), 7.07 (d, J 2.2, 1H), 7.03-6.94 (m, 1H).

후처리

  1. stirringAfter continuing stirring at rt for 15 mins
  2. customreaction mass
  3. extractionextracted with DCM
  4. washDCM layer washed with aq. NaHCO3 and DCM
  5. customremoved on rotavapour
  6. customto obtain the solid
  7. customSolid was triturated with Et2O and Petether mixture (4:1)

출처 및 근거

ORD 기록
ord-0003fc2ae195455e81c9c45022605d5e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181214B2

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