Sodium Carbonate → 2-Formyl-6-naphthylpyridine

HRID 8141

反応式

HRID 8141 の反応式
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[O:28])[N:22]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:27]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:22]=1)=[O:28]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 27570096-Bromopyridine-2-carbaldehyde

生成物 1

HCID 120705612-Formyl-6-naphthylpyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

Naphthylboronic acid (2.06 g, 12 mmol) and Na2CO3 (2.65 g, 25 mmol) were dissolved in 60 mL of degassed 4:1 H2O/MeOH. This solution was added via cannula to a solution of 1.86 g (10 mmol) of 2-bromo-6-formylpyridine and I 16 mg (0.10 mmol) of Pd(PPh3)4 in 50 mL of degassed toluene. The biphasic solution was vigorously stirred and heated to 70° C. under N2 for 4 h. On cooling to RT, the organic phase was separated and washed with 3×25 mL of Et2O. The combined organic extracts were washed with 3×25 mL of H2O and 1×20 mL of brine and dried over Na2SO4. After removing the volatiles in vacuo, the resultant brown oil was chromatographed on silica with 0–50% hexanes/CH2Cl2. The early fractions contained naphthalene and binaphthyl and were discarded. The remaining fractions were combined and the volatiles were removed to provide 2-formyl-6-naphthlypyridine as a white solid.

後処理

  1. customof degassed 4:1 H2O/MeOH
  2. temperatureOn cooling to RT
  3. customthe organic phase was separated
  4. washwashed with 3×25 mL of Et2O
  5. washThe combined organic extracts were washed with 3×25 mL of H2O and 1×20 mL of brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the volatiles in vacuo
  8. customthe resultant brown oil was chromatographed on silica with 0–50% hexanes/CH2Cl2
  9. customthe volatiles were removed
  10. customto provide 2-formyl-6-naphthlypyridine as a white solid

出典と根拠

ORDレコード
ord-ff4c7be6474a4df4bc8cc7292c566b1d
出典データセット
uspto-grants-2006_08
特許番号
US07087690B2

関連ノート

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