Sodium Carbonate → HCID 58464845、化合物

HRID 2089423ノート

反応式

HRID 2089423 の反応式
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[N:18]1([C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[K+]>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(#N)C>[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:25]=2)=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 17982644[3-(Piperidin-1-yl)phenyl]boronic acidHCID 58464823HCID 58464823、化合物

生成物 1

HCID 58464845HCID 58464845、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 6342Acetonitrile溶媒

実験手順

To a microwave reaction vial was added 317 from Example 317 (150 mg, 0.51 mmol), 3-(piperidin-1-yl)phenylboronic acid (312 mg, 1.52 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (41 mg, 0.051 mmol), a 1M solution of Na2CO3 (0.76 mL), a 1M solution of potassium acetate (0.76 mL) and acetonitrile (11 mL). The mixture was irradiated to 120° C. with a microwave for 30 min and cooled to room temperature. It was filtered through Celite and thoroughly washed with methylene chloride. The filtrate was concentrated and the residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide). The product was further purified via reverse phase HPLC to afford 318. 1H NMR (400 MHz, DMSO) δ 10.34 (s, 1H), 8.07 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.71 (s, 1H), 7.59-7.43 (m, 2H), 7.34-7.17 (m, 2H), 7.03-6.84 (m, 3H), 3.83 (s, 3H), 3.26-3.18 (m, 4H), 1.73-1.48 (m, 7H). MS (ESI) m/z: 377.2 [M+H+].

後処理

  1. customTo a microwave reaction
  2. customThe mixture was irradiated to 120° C. with a microwave for 30 min
  3. filtrationIt was filtered through Celite
  4. washthoroughly washed with methylene chloride
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide)
  7. customThe product was further purified via reverse phase HPLC

出典と根拠

ORDレコード
ord-c0b2708c4fc34ba4a5a84ad6b5a3cdbc
出典データセット
uspto-grants-2013_05
特許番号
US08436001B2

反応ノート

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