Ethanol → tert-butyl N-[4-[3-(3-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723106

反応式

HRID 723106 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH3:8].[C:9]([O:13][C:14](=[O:37])[NH:15][C:16]([C:18]1[S:19][C:20]([S:35][CH3:36])=[C:21]([S:23]([C:26]2[CH:31]=[CH:30][C:29](O)=[C:28](B)[C:27]=2O)(=[O:25])=[O:24])[CH:22]=1)=[NH:17])([CH3:12])([CH3:11])[CH3:10].C(O)C.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].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.CCOC(C)=O>[C:9]([O:13][C:14](=[O:37])[NH:15][C:16](=[NH:17])[C:18]1[S:19][C:20]([S:35][CH3:36])=[C:21]([S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[CH3:8])[CH:31]=2)(=[O:25])=[O:24])[CH:22]=1)([CH3:12])([CH3:10])[CH3:11]

参加物

8

反応物 4

HCID 702EthanolHCID 1140TolueneHCID 4283514-Bromo-3-methylpyridineHCID 178419158HCID 178419158、化合物

生成物 1

HCID 145857644tert-butyl N-[4-[3-(3-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate収率 410%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

4-Bromo-3-methyl-pyridine (100 mg, 0.219 mmol, Example 138: step b), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (266 mg, 0.58 mmol, Example 140: step a) and Pd(PPh3)4 (134 mg, 0.12 mmol) were combined in aqueous Na2CO3 (2M, 2 mL), ethanol (2 mL) and toluene (4 mL) and heated to 80° C. overnight. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and the solvent was removed in vacuo. Purification by flash column chromatography (10% DCM/MeOH) afforded the title compound (120 mg, 410%). ESI-MS (m/z): Calcd. for C23H25N3O4S3: 504.1 (M+1); found: 503.7.

後処理

  1. washwashed with brine
  2. dry with materialThe organic layers were dried (MgSO4)
  3. customthe solvent was removed in vacuo
  4. customPurification by flash column chromatography (10% DCM/MeOH)

出典と根拠

ORDレコード
ord-e7d646efbd4648e3b3ddc010c62c5278
出典データセット
uspto-grants-2006_11
特許番号
US07138530B2

関連ノート

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