Sodium Carbonate → Tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate

HRID 241408ノート

反応式

HRID 241408 の反応式
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5](I)=[CH:4][N:3]=1.CC1(C)C(C)(C)OC([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[CH:23]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.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>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)[CH:23]=2)=[CH:6][C:7]=1[CH:8]=[O:9]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 177501772-Amino-5-iodopyridine-3-carbaldehydeHCID 67495092Tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate

生成物 1

HCID 86664806Tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

150 mg (0.605 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 413 mg (1.089 mmol) of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate are dissolved in 2.3 ml of N,N-dimethylformamide in a nitrogen-filled microwave vessel, and 1.7 ml (3.4 mmol) of 2M sodium carbonate solution and 35 mg (0.030 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated to dryness. The oily residue is purified by means of RP-HPLC, giving tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate; HPLC-MS [M+H]+ 372.2.

後処理

  1. additionfilled microwave vessel
  2. customThe reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customThe oily residue is purified by means of RP-HPLC

出典と根拠

ORDレコード
ord-22780cbc61a64bfd8fb8086c92eba15a
出典データセット
uspto-grants-2014_02
特許番号
US08648201B2

反応ノート

読み込み中…