tert-Butanol → HCID 136010275, compound

HRID 2108766Notes

Reaction equation

HRID 2108766 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[S:11][CH:12]=[C:13](C(O)=O)[N:14]=2)=[CH:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.CC[N:37]([CH2:40]C)CC.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:40](=[O:25])[NH:37][C:13]1[N:14]=[C:10]([C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[S:11][CH:12]=1)([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 136010269HCID 136010269, compound

Product 1

HCID 136010275HCID 136010275, compound

Procedure

A mixture of 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazole-4-carboxylic acid (3 g, 12.24 mmol), diphenylphosphoryl azide (4.4 g, 15.91 mmol) and Et3N (4 mL) in tertiary butanol (100 mL) was refluxed for 2 h and cooled to room temperature and concentrated. The residue was dissolved in EtOAC (10 mL) and insoluble material was filtered. The filtrate was chromatographed on silica gel (Biotage) eluting with EtOAc/hexane to give [2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-4-yl]-carbamic acid tert-butyl ester as a off white solid (1.8 g, 46%); Mass Spec; MS 317 (M+1); 1H NMR(DMSO-d6,500 MHz) 12.19 (s,1H), 10.15(s,1H), 8.57(dd,1H),8.32(dd,1H), 8.12(d,1H), 7.23(dd,1H), 7.03(s,1H), 1.49(s,9H).

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAC (10 mL) and insoluble material
  4. filtrationwas filtered
  5. customThe filtrate was chromatographed on silica gel (Biotage)
  6. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-904acdadbbd541c3bd36d6ec5374d5fe
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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