1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761830、化合物

HRID 528586ノート

反応式

HRID 528586 の反応式
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:71][C:72]1[CH:73]=[CH:74][C:75](I)=[C:76]([CH:79]=1)[C:77]#[N:78].CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:71][C:72]1[CH:73]=[CH:74][C:75]([N:20]2[CH2:19][CH2:18][O:17][C:16]3[CH:21]=[C:12]([S:9]([N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]2=3)=[C:76]([C:77]#[N:78])[CH:79]=1

参加物

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70208745-Bromo-2-iodobenzonitrileHCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide2 回

生成物 1

HCID 89761830HCID 89761830、化合物収率 54.2%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

A microwave vial was charged with N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M, 0.320 g, 0.766 mmol), Xantphos (0.089 g, 0.153 mmol), 5-bromo-2-iodobenzonitrile (Combi-Blocks) (0.354 g, 1.150 mmol), Pd2(dba)3 (0.070 g, 0.077 mmol) and sodium tert-butoxide (0.147 g, 1.533 mmol). The mixture was diluted with toluene (7.66 ml), and purged with nitrogen, and stirred at 130° C. in the microwave for 30 minutes, until clean conversion to the desired product. The reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo and the crude material was directly adsorbed onto a 12-g RediSep Gold column and purified by silica gel chromatography, eluting with a gradient of 0% to 100% ethyl acetate in heptane, to provide 4-(4-bromo-2-cyanophenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.248 g, 0.415 mmol, 54.2% yield) as yellow solid.

後処理

  1. custompurged with nitrogen
  2. filtrationThe reaction was filtered over a plug of Celite
  3. washwashing well with DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by silica gel chromatography
  6. washeluting with a gradient of 0% to 100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-cac0ee4a39f1460fbb33c64735544f0f
出典データセット
uspto-grants-2016_05
特許番号
US09346798B2

反応ノート

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