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Hydrochloric Acid → 4-Iodo-2-([1,2]thiazolo[4,5-c]pyridin-7-yl)furo[2,3-c]pyridin-7-amine

HRID 389558
ノート
印刷プレビュー

反応式

HRID 389558 の反応式
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16](B(O)O)[O:15][C:14]=12)=O)(C)(C)C.Br[C:29]1[C:30]2[S:37][N:36]=[CH:35][C:31]=2[CH:32]=[N:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].Cl.C1C(=O)N([I:52])C(=O)C1>CN(C=O)C.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.CO.O.O1CCOCC1>[I:52][C:12]1[CH:11]=[N:10][C:9]([NH2:8])=[C:14]2[O:15][C:16]([C:29]3[C:30]4[S:37][N:36]=[CH:35][C:31]=4[CH:32]=[N:33][CH:34]=3)=[CH:17][C:13]=12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

11

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 120273N-IodosuccinimideHCID 667600997-Bromo[1,2]thiazolo[4,5-c]pyridineHCID 66761297{7-[Bis(tert-butoxycarbonyl)amino]furo[2,3-c]pyridin-2-yl}boronic acid

生成物 1

HCID 667603344-Iodo-2-([1,2]thiazolo[4,5-c]pyridin-7-yl)furo[2,3-c]pyridin-7-amine
収率 57.1%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

A mixture of {7-[bis(tert-butoxycarbonyl)amino]furo[2,3-c]pyridin-2-yl}boronic acid (82.6 mg, 0.219 mmol), 7-bromo[1,2]thiazolo[4,5-c]pyridine (47.0 mg, 0.218 mmol), Pd(PPh3)4 (12.6 mg, 0.0109 mmol), and potassium carbonate (90.6 mg, 0.656 mmol) in 4:1 1,4-dioxane:water (2 mL) was heated to 70° C. for 30 min. Aqueous 12 N hydrochloric acid (0.3 mL, 3 mmol) and methanol (6 mL) was added at 70° C., and the solution was stirred for 2 h. The organic solvents were removed in vacuo, and the material was extracted with DCM and saturated aqueous sodium bicarbonate. The organic layer was purified by column chromatography (1 to 3% 7 N ammonia/methanol:DCM). The purified intermediate was treated with NIS (15.0 mg, 0.0667 mmol) in DMF (1 mL), and the mixture was heated to 40° C. for 20 min. The material was extracted with EtOAc, and washed with aqueous 1 M sodium thiosulfate and brine (2×). The organic layer was concentrated in vacuo to afford 15 mg (17%) of the title compound as a yellow solid. MS (ESI): 395.39 [M+H]+; HPLC tR=1.06 min (HPLC: polar—2 min).

後処理

  1. customThe organic solvents were removed in vacuo
  2. extractionthe material was extracted with DCM and saturated aqueous sodium bicarbonate
  3. customThe organic layer was purified by column chromatography (1 to 3% 7 N ammonia/methanol:DCM)
  4. extractionThe material was extracted with EtOAc
  5. washwashed with aqueous 1 M sodium thiosulfate and brine (2×)
  6. concentrationThe organic layer was concentrated in vacuo

出典と根拠

ORDレコード
ord-6417ab274d0c40d887fa0f719c16d6cf
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08378104B2

反応ノート

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