Cesium carbonate → 5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)-phenyl)picolinonitrile

HRID 525501노트

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HRID 525501 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)O1.[NH2:18][C@H:19]([CH2:29][F:30])[C@@H:20]([C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1)[OH:21].C([O-])([O-])=O.[Cs+].[Cs+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:18][C@H:19]([CH2:29][F:30])[C@@H:20]([C:22]1[CH:23]=[CH:24][C:25]([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)=[CH:26][CH:27]=1)[OH:21]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 45257860(2S,1R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol

생성물 1

HCID 710500475-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)-phenyl)picolinonitrile

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

To a solution of commercially available 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (0.5 g, 2.17 mmol) in degassed dimethoxyethane (10 mL) and water (3 mL) is added (1R,2S)-2-amino-3-fluoro-1-(4-iodophenyl)-propan-1-ol (0.65 g, 2.20 mmol) and Cs2CO3 (2.15 g, 6.6 mmol). Pd(PPh3)4 (0.25 g, 0.21 mmol) is added and the reaction mixture heated to 90° C. for 1.5 hours.

출처 및 근거

ORD 기록
ord-128efe3028614e3b9aba106749f5e592
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340564B2

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