Sodium Bicarbonate → Trifluoroacetic acid

HRID 58080

反応式

HRID 58080 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)O1.Br[C:24]1[CH:25]=[CH:26][C:27]([C:30]([NH2:32])=[O:31])=[N:28][CH:29]=1.[C:33]([O-:36])(O)=[O:34].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:33]([OH:36])([C:18]([F:21])([F:20])[F:19])=[O:34].[F:21][C:18]([F:19])([F:20])[C:16]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][NH:13]2)=[C:9]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([NH2:32])=[O:31])=[N:28][CH:29]=2)[CH:17]=1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 7351515-Bromopyridine-2-carboxamideHCID 897828064-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole

生成物 2

HCID 6422Trifluoroacetic acidHCID 89783150HCID 89783150、化合物

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.05 g, 0.160 mmol), 5-bromopicolinamide (0.042 g, 0.208 mmol) and PdCl2(dppf) (5.86 mg, 8.01 μmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with a gradient of 25-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as an off white solid (19 mg, 0.062 mmol, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (s, 1H), 7.77 (br s, 1H), 8.06 (s, 1H), 8.14-8.33 (m, 1H), 8.37-8.49 (m, 1H), 9.00-9.08 (m, 1H), 13.84 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N4O, 307.1. found 307.15.

後処理

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customthe crude residue was purified by preparative HPLC
  3. washeluting with a gradient of 25-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes
  4. customThe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-b75b16d186f24b88b4b81ea42bb283ed
出典データセット
uspto-grants-2016_09
特許番号
US09434743B2

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