1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(4-methoxybenzyl)-4-(2-(tetrahydro-2H-pyran-4-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528581ノート

反応式

HRID 528581 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.I[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.CC(C)([O-])C.[Na+].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>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]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][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[N:20]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:27][CH:28]=1

参加物

6

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 897614262-(4-Tetrahydropyranyl)iodobenzeneHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

生成物 1

HCID 89761933N-(4-methoxybenzyl)-4-(2-(tetrahydro-2H-pyran-4-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
130 °C

実験手順

A microwave vial was charged N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.120 g, 0.287 μmol), 4-(2-iodophenyl)tetrahydro-2H-pyran (0.124 g, 0.431 μmol), sodium tert-butoxide (0.055 g, 0.575 μmol), tris(dibenzylideneacetone)dipalladium(0) (0.026 g, 0.029 μmol) and xantphos (0.033 g, 0.057 μmol). After purging with N2, toluene (3 mL) was added and the vessel was sealed and heated in the microwave at 130° C. for 30 min. LCMS confirmed coupling product formation. The reaction mixture was concentrated and taken up in DCM, then passed through a 12 g silica gel plug, eluting with 1:1 EtOAC/hex to afford N-(4-methoxybenzyl)-4-(2-(tetrahydro-2H-pyran-4-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a semi-pure orange solid.

後処理

  1. customAfter purging with N2, toluene (3 mL)
  2. additionwas added
  3. customthe vessel was sealed
  4. concentrationThe reaction mixture was concentrated
  5. washeluting with 1:1 EtOAC/hex

出典と根拠

ORDレコード
ord-252bf7dde8ae4795a3a3d19789773b2d
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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