Potassium Phosphate, Tribasic → HCID 68328328、化合物

HRID 634210ノート

反応式

HRID 634210 の反応式
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)([CH3:3])[CH3:2].Cl[C:39]1[CH:44]=[N:43][CH:42]=[C:41]([CH:45]2[CH2:47][CH2:46]2)[N:40]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:45]1([C:41]2[N:40]=[C:39]([C:13]3[C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:7]5[O:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:9][N:8]=5)[CH:11]=4)[N:15]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[CH:14]=3)[CH:44]=[N:43][CH:42]=2)[CH2:47][CH2:46]1

参加物

6

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 649849712-Chloro-6-cyclopropylpyrazineHCID 68328163HCID 68328163、化合物

生成物 1

HCID 68328328HCID 68328328、化合物収率 54%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

To a 20 mL microwave vial was added N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (167 mg, 0.379 mmol), 2-chloro-6-cyclopropylpyrazine (CombiPhos Catalyst Inc., 64.5 mg, 0.42 mmoles), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (10.9 mg, 0.023 mmol), Pd2(dba)3 (10.4 mg, 0.011 mmol), and K3PO4 (242 mg, 1.138 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and H2O (0.4 mL) and heated in the microwave at 120° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification with flash chromatography (eluting with 5-100% EtOAc in Hex) afforded 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (104.4 mg, 54%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 515.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.87 (1H, s), 8.74 (1H, s), 8.42 (1H, s), 8.16 (1H, s), 8.07-8.11 (1H, m), 7.98-8.03 (1H, m), 7.84 (2H, d, J=8.4 Hz), 7.28 (2H, s), 3.97-4.08 (1H, m), 2.36 (3H, s), 2.14 (1H, td, J=8.5, 4.2 Hz), 1.35 (6H, d, J=6.5 Hz), 1.24-1.30 (2H, m), 1.10-1.17 (2H, m).

後処理

  1. customby purging with argon
  2. additionThe solids were treated with dioxane (4.0 mL) and H2O (0.4 mL)
  3. additionThe mixture was treated with H2O
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washwith flash chromatography (eluting with 5-100% EtOAc in Hex)

出典と根拠

ORDレコード
ord-4a74a56750184f49a6f29e478d2961e8
出典データセット
uspto-grants-2016_04
特許番号
US09321756B2

反応ノート

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