Potassium Carbonate → 6-Cyclopropyl-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

HRID 574211ノート

反応式

HRID 574211 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([C:13]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])([CH3:18])[C:14]([F:17])([F:16])[F:15])=[N:11][N:12]=2)[C:5]([NH2:30])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].C([O-])([O-])=O.[K+].[K+].[CH:41]1(B(O)O)[CH2:43][CH2:42]1>O1CCOCC1.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>[CH:41]1([C:2]2[N:7]=[C:6]([C:8]3[O:9][C:10]([C:13]([O:19][Si:20]([CH:21]([CH3:23])[CH3:22])([CH:27]([CH3:28])[CH3:29])[CH:24]([CH3:25])[CH3:26])([CH3:18])[C:14]([F:15])([F:16])[F:17])=[N:11][N:12]=3)[C:5]([NH2:30])=[CH:4][C:3]=2[C:31]([F:32])([F:33])[F:34])[CH2:43][CH2:42]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 867295986-Bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

生成物 1

HCID 867295996-Cyclopropyl-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a stirring solution of 6-bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine (step 3) (200 mg, 0.346 mmol) in dry 1,4-dioxane (10 ml) under N2 at RT was added K2CO3 (144 mg, 1.039 mmol) followed by cyclopropylboronic acid (89 mg, 1.039 mmol) and palladiumtetrakis (40.0 mg, 0.035 mmol). The resulting suspension was stirred and heated at reflux (120° C.) overnight for 4 days. The mixture was filtered through Celite® (filter material) and washed through with water (30 ml) and EtOAc (50 ml). The filtrate was separated and the organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound which was used in the next step without further purification; LC-MS Rt=7.75 min [M+H]+ 539.6 Method 10minLC_v003.

後処理

  1. temperatureheated
  2. filtrationThe mixture was filtered through Celite® (filter material)
  3. washwashed through with water (30 ml) and EtOAc (50 ml)
  4. customThe filtrate was separated
  5. dry with materialthe organic portion was dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ba65951fd97c43e7b5e493c026eb88e8
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

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