Propargyl alcohol → HCID 178432388、化合物

HRID 2120768ノート

反応式

HRID 2120768 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[CH2:25]([OH:28])[C:26]#[CH:27].C(N(CC)CC)C>CN(C=O)C.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>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:24])=[CH:3][C:2]([C:27]#[C:26][CH2:25][OH:28])=[C:11]([CH3:12])[N:10]=3)=[O:14])=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 178432387HCID 178432387、化合物

生成物 1

HCID 178432388HCID 178432388、化合物収率 35.4%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 6-bromo-N-(4-chlorobenzyl)-4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxamide (0.244 g, 0.60 mmol), propargyl alcohol (0.047 g, 0.84 mmol), triethylamine (0.38 mL) and PdCl2(PPh3)2 (0.023 g, 0.03 mmol) in 3 mL DMF is heated to 90° C. for 2.5 h. The resulting solution is cooled and partitioned between EtOAc and water. The solid which formed is filtered and discarded. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2 then 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed to yield 0.081 g (35%) of the desired product as a yellow solid. Physical characteristics are as follows: m.p. 279-281° C. (dec.); 1H NMR (DMSO-d6) δ13.19, 10.12, 8.64, 8.43, 7.38, 5.46, 4.54, 4.40, 2.71; IR (drift) 3194, 3065, 2944, 1645, 1597, 1566, 1522, 1488, 1418, 1357, 1257, 1208, 1015, 851, 809 cm−1; OAMS supporting ions at: ESI+ 381.9 ESI− 379.9; HRMS (FAB) calcd for C20H16CIN3O3 +H1 382.0958, found 382.0960.

後処理

  1. temperatureThe resulting solution is cooled
  2. custompartitioned between EtOAc and water
  3. customThe solid which formed
  4. filtrationis filtered
  5. extractionThe aqueous layer is extracted with EtOAc (3×)
  6. washThe combined organic layers are washed with brine
  7. customdried
  8. customcondensed
  9. customThe crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2
  10. customcondensed

出典と根拠

ORDレコード
ord-9528541ec700436eaa8dd1855d4889d3
出典データセット
uspto-grants-2004_02
特許番号
US06693114B2

反応ノート

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