Potassium Carbonate → HCID 45254510, 화합물

HRID 1970404노트

반응식

HRID 1970404 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C@@:20]3([CH2:24][O:23][C:22]([NH2:25])=[N:21]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:26]#[C:27][C:28]4([CH3:32])[CH2:31][O:30][CH2:29]4)[CH:18]=3)[O:13][C:10]2=[CH:11][CH:12]=1)(=O)=O.[F:35][C:36]1[C:41](B(O)O)=[CH:40][CH:39]=[CH:38][N:37]=1.C(=O)([O-])[O-].[K+].[K+]>CO.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>[F:35][C:36]1[C:41]([C:7]2[CH:8]=[C:9]3[C@@:20]4([CH2:24][O:23][C:22]([NH2:25])=[N:21]4)[C:19]4[C:14](=[N:15][CH:16]=[C:17]([C:26]#[C:27][C:28]5([CH3:32])[CH2:29][O:30][CH2:31]5)[CH:18]=4)[O:13][C:10]3=[CH:11][CH:12]=2)=[CH:40][CH:39]=[CH:38][N:37]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 86640736HCID 86640736, 화합물

생성물 1

HCID 45254510HCID 45254510, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매

실험 절차

A vial was charged with (S)-2′-amino-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (50.0 mg, 0.101 mmol), 2-fluoropyridin-3-ylboronic acid (21.33 mg, 0.151 mmol), potassium carbonate (69.7 mg, 0.505 mmol), and Pd(PPh3)4 (11.66 mg, 10.09 μmol). The vial was flushed with Ar (g), then dioxane (505 μL) and water (0.25 mL) were added in sequence. The vial was sealed and placed in a 70° C. oil for 1 hour. The mixture was diluted with EtOAc and washed with brine. The organic layer was dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 12-g Redi-Sep column with 0-60% of a 90:10:1 mix of DCM/MeOH/NH4OH in DCM to give a pink solid. The solid was dissolved in MeOH and loaded onto a 500-mg SCX-2 column. The column was first eluted with methanol, then with 2N ammonia in methanol to remove the product. The filtrate was evaporated to give (S)-7-(2-fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine as pale yellow solid. Found MS: MH+=443.0.

후처리

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (505 μL) and water (0.25 mL) were added in sequence
  3. customThe vial was sealed
  4. customplaced in a 70° C.
  5. customfor 1 hour
  6. additionThe mixture was diluted with EtOAc
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was chromatographed on a 12-g Redi-Sep column with 0-60% of a 90:10:1
  12. additionmix of DCM/MeOH/NH4OH in DCM
  13. customto give a pink solid
  14. washThe column was first eluted with methanol
  15. customwith 2N ammonia in methanol to remove the product
  16. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-6b2787d7336d46a0896aa751a3790831
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426447B2

반응 노트

불러오는 중…