Triphenylphosphine → 1-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea

HRID 9124ノート

反応式

HRID 9124 の反応式
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1S(C(F)(F)F)(=O)=O.[Cl-].[Li+].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.[CH:45]([Sn](C=C)(C=C)C=C)=[CH2:46].[Sn]>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:26]([C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[CH:45]=[CH2:46])=[CH2:27]

参加物

8

反応物 5

HCID 11776TriphenylphosphineHCID 66189TetravinylstannaneHCID 433294Lithium ChlorideHCID 5352426Tin atomHCID 219855071-(6-Bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea

生成物 1

HCID 219856411-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea収率 39.4%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

Similar to the synthesis of Example 203, a mixture of 1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.22 mmol), lithium chloride (0.078 g, 1.84 mmol, 8.4 eq), triphenylphosphine (0.034 g, 0.13 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.018 g, 0.026 mmol, 0.12 eq), tetravinyltin (0.080 mL, 0.44 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 18 hours. Additional tin reagent (0.080 mL, 0.44 mmol, 2.0 eq) was added to the mixture after the first 2 hours. The mixture was taken up in MeOH, filtered, and concentrated. Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4) gave the desired compound 0.014 g (23%). LC/MS 274.3 (M+1); LC retention time 2.32 min.

後処理

  1. customSimilar to the synthesis of Example 203
  2. customa crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4)

出典と根拠

ORDレコード
ord-43344259a13143f2b751032583d652d5
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

反応ノート

読み込み中…