Phosphoric Acid → 1H-Indol-6-ylboronic acid

HRID 216185

反応式

HRID 216185 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[B:16](OCCCC)([O:22]CCCC)[O:17]CCCC.P(=O)(O)(O)O>CCOCC>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([B:16]([OH:22])[OH:17])[CH:10]=2)[CH:6]=[CH:7]1

参加物

6

反応物 4

HCID 1004Phosphoric AcidHCID 12712Tributyl borateHCID 6764936-BromoindoleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 27632051H-Indol-6-ylboronic acid

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 6-bromoindole (200 mg, 1.02 mmol) in anhydrous ether (4 mL), at −78° C., is treated dropwise with tert-butyllithium (1.7 M solution in pentane, 2 mL, 3.4 mmol). After stirring for 30 minutes the mixture is treated dropwise with tributyl borate (0.822 mL, 3.06 mmol) and allowed to warm up to room temperature. After stirring overnight the reaction mixture is diluted with ether, and this mixture is added in portions to phosphoric acid (15 mL, 1M), stirred for 30 minutes and extracted three times with ether (20 mL). The combined extracts are extracted three times with sodium hydroxide solution (20 mL, 1N). The combined sodium hydroxide extracts are acidified with phosphoric acid (1 M) to pH=2, extracted with ether. The combined ether extracts are washed with brine, dried over sodium sulfate and concentrated to obtain 1H-indol-6-yl-boronic acid [Intermediate (77)] as a solid, which is used for the next step without further purification.

後処理

  1. stirringAfter stirring overnight the reaction mixture
  2. stirringstirred for 30 minutes
  3. extractionextracted three times with ether (20 mL)
  4. extractionThe combined extracts are extracted three times with sodium hydroxide solution (20 mL, 1N)
  5. extractionextracted with ether
  6. washThe combined ether extracts are washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c59cc83136d0472ebf08a7048a01d54f
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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